Methylene-disalicylic acid derivative



Patented Jan. 14, 1930 SAMUEL LEWIS-SUMMERS, OF FORT WASHINGTON, PENNSYLVANIA METHYLENE-DISALICYLIC ACID DERIVATIVE No Drawing.

My invention relates to organic compounds and'their manufznture and is especially con cerned with an iodination product of methylene-disalicylamide. This substance is useful for pharmaceutical purposes as hereinafter indicated.

The first main step is to convert methylenedisalicylic acid into one of its esters. As the alcohol is removed in the next step the particular nature-of the'alcohol is of little consequence. ()ne way of esterifying this acid is as follows, though I do not limit myself to this particular method:

Dissolve 288 pounds of methylene-disalicylic acid in 150 pounds of ethyl alcohol and slowlv add to this solution, while keeping the ten'iperature at 70 C., a mixture of 60 parts of 66 B. sulphuric acid and 40 parts of water. lVhen all has been added, heat for 2 two hours under a reflux condenser to 150 C. The product is freed from sulphuric acid by washing with water. The essential product is the diethyl ester of methylene-disalicylic acid:

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c on 00 H CH/ s i( N a I oumomoonm This is purified by washing with water, in which it is insoluble. It is a cream colored powder soluble in alcohol.

The third main step is to iodinate this methylene-disalicylamide. A practical way (to which I do not limit myself) for accomplishing this is to dissolve 286 parts of the 0 methylene-disalicylamide' in 286 parts of product of methylene-disalicylamide,

' Application filed December 8, 1928. Serial N o. 324,804.

26% aqueous ammonia and add to this solution a solution of 254 parts of iodine and 381 parts of potassium iodide in 500 parts of water. After the reaction is complete, an acid (sulphuric or other strong acid) is added to decompose the partly dissolved and partly precipitated alkaline salts. This sets free the iodinated methylene-disalicylamide, which separates as an amorphous precipitate. This is filtered 01f, washed with water to free it from acid and soluble salts, and dried. The empirical formula for complete iodination is C H O N I and the structural formula is thought to be:

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CONH:

However, it will be understood that iodination may involve only one ring of the methylene-disalicylamide. This new rod- 7 not is practically tasteless, insolub e in water, and only slightly soluble in alcohol. It is useful as an antiseptic, antineural'gic, antiarthritic, antirheumatic and dicongestive. The dose for an adult may be from 90 to 120 grains per day.

Having thus described my invention, I claim:

1. The herein described iodine substitution product of methylene-disalicylamide having 35 one or two nuclear hydrogens replaced by iodine, insoluble inwater and slightly soluble in alcohol.

2. The herein described iodine substitution having the empirical formula C H O N I insoluble in water, and slightly soluble in alcohol.

In testimony whereof, I have hereunto signed my name at Ambler, Pennsylvania this 4th day of December, 1928.

SAMUEL LEWIS SUMMERS. 

